Born in Brixton, Shakes began his career at Bolton Wanderers in 2004 and made his debut in an FA Cup third-round replay against Tranmere Rovers in January 2004, scoring a last-minute equaliser to take the match into extra time. He failed to make a league appearance for Bolton, and after spells on loan with Bristol Rovers and Bury, joined Swindon Town in July 2005. Shakes made almost 70 league appearances in two seasons at Swindon but was released at the end of the 2006–07 campaign.

He joined Brentford in August 2007 after training with the club during the summer and scored a late goal on his debut in September 2007 to give Brentford victory at Bury. After making 39 league appearances, Shakes was released at the end of the 2007–08 season.

He joined Conference Premier club Ebbsfleet United in July 2008. Having scored 11 goals for Ebbsfleet, he added to that statistic by scoring eight goals in 40 league appearances for the club during the 2011–2012 season. On June 28, 2012, Shakes signed for Kidderminster Harriers and made 17 appearances helping the club finish second in the Conference Premier.

On July 3, 2013, Shakes made the switch to Boreham Wood, with the club fighting off stiff competition from several other clubs.

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